I was that kid who refused to sell crap door to door to raise money for a new choir robe . I’d just as soon babysit as sell smelly candles. But even with babysitting, I hated choosing a rate, hated asking for money, and absolutely loathed people who made me calculate how much they owed.

So it is no surprise that I also hate invoicing as an adult. I probably have some sort of deep issue with money, but I know I’m not alone.

One of the challenges of having your own small business is staying on top of the financial paperwork, but, of course, if you don’t, then you will soon have no money. I now have a high-tech spreadsheet to calculate everything from total billed, to total owed, to taxes owed courtesy of Ghost Girl. This is a good thing. But I still have to bill.

Here’s a summary of the top challenges gleaned from my experience and that of my many freelancing friends*:

1. Every client wants the invoice to appear in a different format, often with a standard template that they have designed. It is important for the template only to be accessible in an obscure software program. If it happens to be in Word or Excel, it usually contains cryptic blanks with “Fill In Here” in Gaelic.

2. Often there are 2-5 secret codes that freelancers or contractors need to complete the invoice. These may be in the contract. They should be in the contract. They may also be in one of the 10,000 emails in the in-box about this project.

3. Once the invoice is sent, it disappears into a Void. Never is any sort of receipt sent, unless, of course, the invoice is rejected. This Void (also know as the Invoicing Void of Despair) is a dark place, my friends, where paper goes and never returns.

4. If there is a “problem” with the invoice, often it is not reported until payment time has elapsed. This is because some accounting departments seem to wait the maximum number of days to pay until there is threat of small claims court looming. We know they are overworked. As are all of us.

5. Here’s a final problem. Tracking down money takes time. And it takes time away from billable working. This is why people hire someone to do it for them. Because from making the invoice to recording the invoice to tracking the invoice to following up when the invoice is lost….time is spent and not necessarily well spent unless it results in payment.

I think this is one of those issues that just is. As in, it simply exists. There is nothing to do to change it. It is the nature of having your own business. Your thoughts?

*Note that there are clients who pay well and regularly and we are blessed to be in their service.